Paclitaxel

Paclitaxel
Clinical data
Trade names	Taxol, Abraxane, others
Other names	PTX
AHFS/Drugs.com	Monograph
MedlinePlus	a607070
License data	EU EMA: by INN; US DailyMed: Paclitaxel;
Pregnancy; category	AU: D;
Routes of; administration	Intravenous
ATC code	L01CD01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	6.5% (by mouth)
Protein binding	89 to 98%
Metabolism	Liver (CYP2C8 and CYP3A4)
Elimination half-life	5.8 hours
Excretion	Fecal and urinary
Identifiers
	IUPAC name (2α,4α,5β,7β,10β,13α)-4,10-Bis(acetyloxy)-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate;
CAS Number	33069-62-4 ;
PubChem CID	36314;
IUPHAR/BPS	2770;
DrugBank	DB01229 ;
ChemSpider	10368587 ;
UNII	P88XT4IS4D;
KEGG	D00491 ;
ChEBI	CHEBI:45863 ;
ChEMBL	ChEMBL428647 ;
PDB ligand	TA1 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID9023413 ;
ECHA InfoCard	100.127.725
Chemical and physical data
Formula	C47H51NO14
Molar mass	853.918 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C2[C@@]([C@]([C@H]([C@@H]3[C@]4([C@H](OC4)C[C@@H]([C@]3(C(=O)[C@@H]2OC(=O)C)C)O)OC(=O)C)OC(=O)c5ccccc5)(C[C@@H]1OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7)O)(C)C;
	InChI InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1 ; Key:RCINICONZNJXQF-MZXODVADSA-N ;
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Paclitaxel, sold under the brand name Taxol among others, is a chemotherapy medication used to treat ovarian cancer, esophageal cancer, breast cancer, lung cancer, Kaposi's sarcoma, cervical cancer, and pancreatic cancer. It is administered by intravenous injection. There is also an albumin-bound formulation.

Common side effects include hair loss, bone marrow suppression, numbness, allergic reactions, muscle pains, and diarrhea. Other side effects include heart problems, increased risk of infection, and lung inflammation. There are concerns that use during pregnancy may cause birth defects. Paclitaxel is in the taxane family of medications. It works by interference with the normal function of microtubules during cell division.

Paclitaxel was isolated in 1971 from the Pacific yew and approved for medical use in 1993. It is on the World Health Organization's List of Essential Medicines. It has been made from precursors, and more recently through cell culture.

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